CHEM 2212 Organic Chemistry II - Summer 2009Laboratory Program

Course Goal

Exp Obj

Experiment Objective Description Assignment

Exp H. Preparation of Aldehydes and Ketones by Oxidation of Alcohols: Oxidation of 4-Chlorobenzyl Alcohol to 4-Chlorobenzoic Acid 8-14

DatesJan 14Jan 28

h1 Conduct an oxidation of an alcohol to a carboxylic acid.

1. Read: pp. 525-530 (oxidation of alcohols); pp. 535-537-chlorobenzyl alcohol and microscale procedures)2. Complete Exercises: pp. 538-539 questions 2, 3, 4, 10, 15

h2 Isolate the product.h3 Characterize and analyze.h4 Present, analyze, and discuss results in a written

report.Exp I. Reactions of Carbonyl Compounds: Synthesis of (Z)- and (E)-Stilbenes by a Wittig Reaction 8-14

DatesFeb 4Feb 11

i1 Synthesize a mixture of stilbenes by a phase-transfer Wittig reaction.

1. Read: pp. 585-589 (Wittig reaction); pp. 590-593 (synthesis of stilbenes and microscale procedures)2. Complete Exercises: pp. 596-598 questions 3, 6, 12, 14

i2 Isolate the product.i3 Characterize and analyze.i4 Present, analyze, discuss results in written a report.

Exp J. Aldol Condensations to Produce α,β-unsaturated Carbonyl Compounds: Synthesis of trans-p-Anisalacetophenone 8-14

DatesFeb18Feb 25

j1 Synthesize an α,β-unsaturated carbonyl compound. 1. Read: pp. 601-603 (aldol condensations); pp. 603-605 (trans-p-anisalacetophenone and microscale procedures)2. Complete Exercises: pp. 605-606 questions 2, 6, 7, 13

j2 Isolate the product.j3 Characterize and analyze.j4 Present, analyze, and discuss results in written a

report.Exp K. Fischer Esterification Reaction of a Carboxylic Acid Derivative: Preparation of Benzocaine 8-14

DatesMar 3Mar 17

k1 Conduct an acid-catalyzed esterification of a carboxylic acid with an alcohol.

1. Read: pp. 651-655 (Fischer esterification); pp. 655-658 (preparation of benzocaine and microscale procedures)2. Complete Exercises: pp. 658-659 questions 7, 11

k2 Isolate the product.k3 Characterize and analyze.k4 Present, analyze, and discuss results in written a

report.Exp L. Preparation of Amides from Carboxylic Acid via Acid Chloride: Preparation of N,N-Diethyl-m-toluamide (DEET) - NEED TO KNOW GLASSWARE SETUP BEFORE COMING TO LAB!8-14

DatesMar 24Mar 31

l1 Conduct synthesis of an amide from a carboxylic acid via the corresponding acid chloride.

1. Read: pp. 661-663 (amides and insect repellents); pp. 664-668 (preparation of N,N-diethyl-m-toluamide and microscale procedures)2. Complete Exercises: pp. 668-669 question 12

l2 Isolate the product.l3 Characterize and analyze.l4 Present, analyze, and discuss results in a written

report.

Exp M. Synthesis Exam 5

DateApr 7

m1 Understand and apply techniques to synthesize organic molecules.

All course material

Exp N. Qualitative Identification of Organic Compounds by Functional Group Differentiation 15

DateApr 14

n1 Use qualitative functional group tests to identify and match 6 unidentified compounds to a list of 6 known compounds.

1. Read: pp. 817-821 (qualitative analysis); pp. 867-868 (ceric nitrate test for alcohols); pp. 840-842 (2,4-DNP test for aldehydes and ketones); pp. 844-846 (chromic acid test for 1o/2o alcohols and aldehydes); pp. 846-848 (iodoform test for aldehydes and ketones with α-hydrogen); pp. 843-844 (Tollen’s test for aldehydes); pp. 851-852 (bromine test for unsaturation); pp.853-854 (silver nitrate test for alkyl halides)

All experiments: 1. are microscale.2. are 2 laboratory sessions of 3 hours each for a total of 6 hours per experiment, except Exp M & N, which are 3 hours each.3. have assignments refer to Gilbert and Martin, Experimental Chemistry: a Miniscale and Microscale Approach, 4th ed. (except as noted).

CHEM 2212 Organic Chemistry II - Summer 2009Laboratory Program